Black disazo cotton dye



Patented July AUGUST LEOPOIQD LASKA AND ARTHUR ZITSCHER, OF OFFENBACH-ON-THE-MAJJT,

GERMANY, ASSIGNORS TO THE CORPORATION OF CHEMIBCHE FABRIK GBIESKEIH- ELECTRON, OF FRANKFORT-ON-THE-MAIN, GERMANY.

PATENT OFFICE.

BLACK DISAZO COTTON DYE.

No Drawing. Application filed April 2, 1924, Serial No. 708,747, and in Germany April 17, 1828. In our U. S. Patent No. 1,452,083 dated April 17, 1923,

we have described black azodyestuffs, which are formed by combining the diazocompound of an aryl-azo-l-naphgroup) with an naphthoic acid.

thylamin compound Snot containing a sulfo ary amid of 2.3-hydroxy- Now we have found, that valuable black azodyestufls yielding, when mixed with the usual substrate, black pigment colors and,

when produced on the fiber, dyeing cotton in black shades of an excellent fastness are obtained by combining the diazocompounds of unsulfonated aryl-azo-l-naphthylamin bodies, containing basic groups in one or several lateral chains either in the aryl or in the naphthalene residue or in both, with ar lamids of 2.3-hydroxynaphthoic acid.

Vhen referring above to the usual substrata we mean substrata, such as barium sulfate or aluminum hydroxide, which are customarily employed in the production of pigment colors.

These dyestufi's probably have the general formula:

YNHO

wherein S means a basic group such as Alkyl Alkyl Alkyl Alkyl Alkyl With other 80 naphthylamin b cormspondin odies and ot er aryl-azo-lsitions simultaneously, X the residue of an l-naphthylamin compound capable of combining in the 4-posit1on and not contai a sulfo group, Y an aromatic radical. These dyestufi's are when 11x31!1 black powders, yielding upon reduction wit stannous chlorid an arylamin containing 0 to 2 basic groups in lateral chains, an 1.4-diamin0- compound of the naphthalene series, containing 0 to 2 basic groups in lateral chains, and an arylid of 1-amino-2-hydroxy-3- 5o naphthoic acid.

The presence of a basic group in external binding works advantageously upon the solubility of the diazocompounds, so that by means of the above mentioned aminoazocompounds the preparation of stronger concentrated solutions, as are used for adding subsequently to the developing-baths, is really facilitated.

The following example illustrates the invention, the parts being by weight.

Ewample.

The cotton yarn, well boiled and dried, in impre nated with a solution of 4 gr. of 05 B-nap thalid of 2.3-hydroxynaphthoic acid 15 cc. of caustic soda solution of 34 B. and 20 cc. of Turkey red oil per liter, wrun out as well as possible and developed wit out drying in a diazo solution, containing 6.5 g. of the aminoazo body from diazotized 4- aminobenzyldimethylamin and l-naphthylamin per liter, to which sodium acetate has been added, rinsed and soaped.

In this manner bluish black shades of an excellent fastness are obtained. The dyestufi thus produced probably has the following formula:

of 2.3-hydroxynaphthoic acid the process arylamids may be conducted in the same manner.

The-following table gives the shades of a number of dyestufis, prepared according to the present process:

Combined with the Dino compound ary1ido!2.3h shaman 11:10am body wg f Shades.

1. 4-amiuobenzy1di- Anilid Iluiah black. methy a-naphth lamin 2 Dop.1 Exam- B-napbthaiid Do.

0. 8. Do Para-anisidid Do. 4. Do Meta-chloroanilid--- R lshblack. 5. e-emino-u-dimeth- Meta-nltroanilid..- Bl black.

ylamlnophenethol-i-u-naphthgamin. o B-naphthalid Do. 7. Do Memhloroanllid... Violet-black. I. Hminobenzyldi- Mete-niu'oanllid.... Do.

moth lamin+ a-na thylamln.

The final dye enumerated above under 6 The final dye enumerated above under 12 gyamfj The final dye enumerated above under 16 on on orcm ca -c Now what we claim and desire to secure by Letters Patent is the following:

1. As new articles the black azodyestufis; 40 having probably the general formula:

YNHO 0 wherein S means a basic grou n the number 0, 1 or 2, but not 0 in bot positions si- The final dye enumerated above under 4 35 probably has the following formula:

01 ONE-0C no probably has the following formula:

probably has the following formula:

Cl-QHN-CO o m no probably has the formula:

cunoONn-oc multaneously, X the residue of an l-naphthylamin compound capable of combining in the 4-position and not containin a sulfo group, Y an aromatic radical, w ich are when dry black powders, yielding upon reduction with stannous chlorid an arylamin containing 0 to 2 basic groups in lateral chains, an 1.4-diaminocompoun'd of the naphthalene series containing 0 to 2 basic groups in lateral chains and an arylid of 1- amino-2-hydroxy-3-na hthoio acid, said dyestufis, when mixe with the usual subcontainin strata, producing black color lakes and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

2. A process of making black azodyestufis consisting in combinin unsulfonated arylazo-l-naphthylamin b0 ies containing basic groups with arylamids of 2.3-hydroxynaphthoic acid.

3. Materials dyed with the new azodyestufi's according to claim 1, said dyestuffs being developed on the fiber of the material.

4. As new articles the black azodyestufi's, having probably the general formula:

YNHOC wherein S means a basic group, X the residue of an l-naphthylamin com ound capable of combinin in the 4-posit1on and not a su f0 rou Y an aromatic radical, w ich are w on 'ry black powders, yielding u on reduction with stannous chlorid an ary amin containing a basic grou in a lateral chain, an 1.4-diaminooompoun of the naphthalene series and an a lid of L amino-2-hydroxy-3-naphthoic aci ,said dyestuffs, when mixed with the usual substrata, producing black color lakes and, when produced on the fiber, dyeing cotton in b ack shades of an excellent fastness.

5. A process of making black azodyestufls consistin in combinin unsulfonated arylazo-l-nap thylamin b0 ies containin inthe aryl residue :1 basic group in a lateral chain, with arylamids of 2.3 hydroxynaphthoic acid.

6. Materials dyed with the new azodyestufis according to claim 4, said dyestufl's being develope on the fiber of the material.

7. As new articles the black azodyestufl's,

having probably the general formula:

Gem-N =N X- N=N E0 (Hr-NUDE:

YNHOC wherein X means the residue of an l-naphthylarnin compound capable of combining in the 4- osition and not containin a sulfo group, an aromatic radical, \v 1ich are when dry black powders, yielding upon reduction with stannous chlorid aminobenzyldimethylamin, an 1.4-diaminocompound of the naphthalene series and an arylid of 1' amino-2-.hydroxy-3-nnphthoic acid, said dyestuffs, when mixed with the usual substrate, producing black color lakes and, when roduccd on the fiber, dyeing cotton in b ack shades of an excellent fastness.

8. A process of making black azodyestufl's consisting in combining unsulfonated benzyldimenthylaminaao-l-na hthylamin bodies with arylamids of 2.3- ydroxynaphthoic aci 9. Materials dyed with the new azodyestuffs accordin to claim 7, said dyestuffs being develope -on the fiber of the material.

10. As new articles the black azod estuils, having probably the general formula:

l no

H:N(CH|)1 Naphthyl-HNO wherein X means the residue of an -1-naphthylarnm compound capable of combining in the 4-position and not containing a sulfo grou which are when dry black powders, yiel mg upon reduction with stannous chlorid aminobenz ldimethylamin an 1.4-diaminocompoun of the naphthalene series and a naphthalid of 1amino-2-hydrox y-3- naphthoic acid, said dyestufl's, when mixed with the usual substrate, producing black color lakes and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

11. A process of making black azodyestuffs consisting in combining unsulfonated benzy ldimethylamin-azo 1 naphthylamin bodies with naphthalids of 2.3-hydroxynaphthoie acid.

12. Materials dyed with the new azodyestufl's accordin to claim 10, said dyestufls being develope on the fiber of the material.

In testimony, that we claim the foregoing as our invention, we have signed our names, this 13th da of March, 192

' A GUST LEOPOLD LASKA.

ARTHUR ZITSOHER.

eontainin strata, producing black color lakes and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

2. A process of making black azodyestufl's consisting in combining unsulfonated arylazo-l-naphthylamin bodies containing basic groups with arylamids of 2.3-hydroxynaphthoic acid.

3. Materials dyed with the new azodyestufi's according to claim 1, said dyestuffs being developed on the fiber of the material.

4. As new articles the black azodyestufi's, having probably the general formula:

YNHOC wherein S means a basic group, X the residue of an l-naphthylamin com ound capable of combinin in the 4-posit1on and not a su to group, Y an aromatic radical, w ich are when dry black powders, yielding upon reduction with stannous chlorid an arylamin containing a basic group in a lateral chain, an lA-diaminocompound of the naphthalene series and an arylid of 1- amino-Q-hydroxy-3-naphthoic acid, said dyestuffs, when mixed with the usual substrate, producing black color lakes and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

5. A process of making black azodyestufls consisting in combinin unsulfonated arylazo-l-naphthylamin bo ies containing in the aryl residue a basic group in a lateral chain, with arylamids of 2.3 hydroxynaphthoic ael 6. Materials dyed with the new azodyestufis according to claim 4, said 'dyestufls being developed on the fiber of the material.

7. As new articles the black azodyestufi's, having probably the general formula:

HO LHr-NwHlh YNHOC wherein X means the residue of an l-na hthylamin compound capable of combining in the 4-position and not containing a sulfo group, Y an aromatic radical, which are when dry black powders, yielding upon reduction with stannous chlorid aminobenzyldimethylamin, an 1.4-diaminocompound of the naphthalene series and an arylid of 1- amino-Q-hydroxy-3-naphthoic acid, said dyestuffs, when mixed with the usual substrata, producing black color lakes and, when produccd on the fiber, dyeing cotton in black shades of an excellent fastness.

8. A process of making black azodyestufi's consisting in combining unsulfonated benzyldimenthylaminazo-l-naphthylamin bodies with arylamids of 2.3-hydroxynaphthoie acid.

9. Materials dyed with the new azodyestuffs according to claim 7, said dyestuffs being developed on the fiber of the material.

10. As new articles the black azodyestufi's, having probably the general formula:

i so

H:N[ 0 HI),

Naphthyl-HNO wherein X means the residue of an l-naphthylamin compound capable of combining in the 4-position and not containing a sulfo group, which are when dry black powders, yielding upon reduction with stannous chlorid aminobenzyldimethylamin, an 1.4-diaminocompound of the naphthalene series and a naphthalid of 1-amino-2-hydroxy-3- naphthoic acid, said dyestufl's, when mixed with the usual substrate, producing black color lakes and, when produced on the fiber, dyeing cotton in black shades of an excellent fastness.

11. A process of making black azodyestufl's consisting in combining unsulfonated benzyldimethylamin-azo 1 naphthylamin bodies with naphthalids of 2.3-hydroxynaphthoic acid.

12. Materials dyed with the new azodyestufl's accordin to claim 10, said dyestufl's being 'develope on the fiber of the material.

In testimony, that we claim the foregoing as our invention, we have signed our names, this 13th day of March,1924.

AUGUST LEOPOLD LASKA. ARTHUR ZITSCHER.

Certificate of Correction. It is herebv certifiedthat Letters Patent No. 1,592,604, granted July 13. 1926.

upon the application of August Leopold Laska and on-the-Main, Germany, for an improvement in Corporation of Chemische Fabrik Griesheim-Electron, 1 whereas said Letters Patent should have been issued to Aktienyeswl/scbaff, Franl'forf-on-the-Main, Germany, as in this ofiice; and that the said Letters Patent erroneously issued to the of F rankfort-on-the-l\ lain. I. G. Farbcnindust'rz'e shown by the records of assignments Arthur Zitscher, of Offenbach- Black Disazo Cotton Dyes," were should be readnvith this correction therein that the same may conform to the record of the case in the Patent Oflice.

Signed and sealed this 19th day of October, A. D. 1926.

[sun] WM. A. KIN N AN Acting Commissioner of Patents Certificate of Correction.

t is hereby certified that Letters Patent No. 1.5921304 granted July 13. 192(L upon the application of August Leopold Laskn and Arthur Zitschcr. of Oil'cnhach- On-the-Main, Germany, for an improvementin Black DiSuzo Cotton Dyes? wcrc erroneously issued to the Corporation of Chcinische Fuhrik Griesheim-Electron, of Frankfort-oilfile-Main, whereas said Letters Patent should have been issued to I. G. Farbcn'iudustrz'e AktiengescI/sc/mff. Frankfort-0nJim-Main. (rcrmmry, as shown by the records of assignments in this ofiice; and that the said Lem-rs Piitcnt should be readjvith this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 19th day of ()ctobcr, A. D. 1926.

[emu] \VM. A. KINNAN,

Acting Commissioner of Patents 

